Bromine → 3-Bromo-5-chloropyridin-2-amine

HRID 231531Notes

Reaction equation

HRID 231531 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.[Br:9]Br>C(Cl)Cl>[NH2:1][C:2]1[C:7]([Br:9])=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 661742-Amino-5-chloropyridine

Product 1

HCID 27639713-Bromo-5-chloropyridin-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

20 g (77.8 mmol) of 2-amino-5-chloropyridine dissolved in 160 ml of CH2Cl2 are reacted with 8 ml of bromine, which is added dropwise at 0° C. After the addition is complete, the mixture is left to react at 25° C. for 2 h. The suspension is washed with 10% strength sodium hydroxide solution, and the organic phase is washed with water and then dried over MgSO4, filtered and evaporated. The compound obtained is recrystallized in isopropanol. M.p. 82° C.

Workup

  1. additionis added dropwise at 0° C
  2. additionAfter the addition
  3. waitthe mixture is left
  4. customto react at 25° C. for 2 h
  5. washThe suspension is washed with 10% strength sodium hydroxide solution
  6. washthe organic phase is washed with water
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customThe compound obtained
  11. customis recrystallized in isopropanol

Sources & evidence

ORD record
ord-3451f38d55ba4813800da4d87e3bf5b8
Source dataset
uspto-grants-1989_07
Patent number
US04847263

Reaction notes

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